Hydrochloric Acid → Gatifloxacin

HRID 1594379Notes

Reaction equation

HRID 1594379 reaction equation
[CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[C:13]([O:14][CH3:15])=[C:12]3[N:16]([CH:24]4[CH2:26][CH2:25]4)[CH:17]=[C:18]([C:21]([OH:23])=[O:22])[C:19](=[O:20])[C:11]3=[CH:10][C:9]=2[F:27])[CH2:3]1.Cl.[OH-].[Na+].Cl>C(#N)C.O>[CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[C:13]([O:14][CH3:15])=[C:12]3[N:16]([CH:24]4[CH2:26][CH2:25]4)[CH:17]=[C:18]([C:21]([OH:23])=[O:22])[C:19](=[O:20])[C:11]3=[CH:10][C:9]=2[F:27])[CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 17956339Gatifloxacin hydrochloride

Product 1

HCID 5379Gatifloxacin

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
5 °C

Procedure

Gatifloxacin-HCl (10 g) was suspended in 60 mL of a mixture of acetonitrile:H2O (90:10). The suspension was cooled to 5° C. At this an aqueous solution of NaOH 47% (0.7 eq) was added to neutralize the hydrochloride. The mixture was stirred at 5° C. for 1 hour and then the precipitate was collected by filtration and washed with the aqueous mixture (10 mL) ACN:H2O (90:10). The solid was dried under vacuum at 50° C. overnight. The solid was analyzed by XRD and found to be form Y.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with the aqueous mixture (10 mL) ACN:H2O (90:10)
  3. customThe solid was dried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-8b8e2d76648c4531b7b69ca0dc7b0171
Source dataset
uspto-grants-2007_11
Patent number
US07301024B2

Reaction notes

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